dentatin | 22980-57-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: dentatin
• 英文别名: poncitrin；Dentatin , Poncitrin；5-methoxy-2,2-dimethyl-10-(2-methylbut-3-en-2-yl)pyrano[3,2-g]chromen-8-one
• CAS: 22980-57-0
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: QBFYQVZGIDUNIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dentatin 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 以90.7%的产率得到Tetrahydroponcitrin
  参考文献：
  名称：

  Anti-HBV and cytotoxic activities of pyranocoumarin derivatives

  摘要：

  Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human cancer cell lines (A549, MCF7, KB, and KB-VIN). To explore the SAR of 1-4, 17 pyranocoumarin analogues (5-21) were designed and synthesized. Among these analogues, 5 and 10 were the most potent against hepatitis B virus with EC50 values of 1.14 and 1.34 mu M, respectively. The most interesting result in the cytotoxicity assay was the significant activity of 1, 5, and 6 against the multi-drug resistant cell line, KB-VIN, without activity against the KB cell line. These data suggest that these three compounds could be useful hits for developing MDR-inverse drugs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.007
• 作为产物：
  描述：

  5-acetoxy-6-(1,1-dimethylallyl)seselin 在 甲醇 、 sodium hydroxide 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 53.5h， 生成 dentatin
  参考文献：
  名称：

  Claisen rearrangements-XIII

  摘要：

  DOI：

  10.1016/s0040-4020(01)82439-x

文献信息

• Constituents of Domestic Citrus Plants. Part XVI. Five New Pyranocoumarins from Some Citrus Plants.
  作者：Yuko TAKEMURA、Yumiko NAKATA、Miki AZUMA、Motoharu JU-ICHI、Masayoshi OKANO、Narihiko FUKAMIYA、Mitsuo OMURA、Chihiro ITO、Kiyomi NAKAGAWA、Hiroshi FURUKAWA

  DOI：10.1248/cpb.41.1530

  日期：——

  Five new pyranocoumarins, named cis-5-methoxydecursidinol (1), trans-5-methoxydecursidinol (2), cis-hassanin (4), trans-hassanin (5), and hassanidin (7), were isolated from the roots of some Citrus plants and their structures were elucidated by spectroscopic methods and chemical derivation from known coumarins.

  从一些柑橘类植物的根中分离出了五种新的吡喃香豆素，分别命名为顺式-5-甲氧基癸基香豆素醇（1）、反式-5-甲氧基癸基香豆素醇（2）、顺式-哈萨宁（4）、反式-哈萨宁（5）和哈萨宁（7），并通过光谱方法和已知香豆素的化学衍生方法阐明了它们的结构。
• Efficient syntheses of the coumarins, nordentatin, dentatin and clausarin
  作者：R.D.H. Murray、Z.D. Jorge

  DOI：10.1016/s0040-4039(00)94531-3

  日期：1983.1
• Anti-HBV and cytotoxic activities of pyranocoumarin derivatives
  作者：Chung-Ren Su、Sheau Farn Yeh、Chih Miem Liu、Amooru G. Damu、Tsung-Hsiao Kuo、Po-Cheng Chiang、Kenneth F. Bastow、Kuo-Hsiung Lee、Tian-Shung Wu

  DOI：10.1016/j.bmc.2008.12.007

  日期：2009.8

  Four natural pyranocoumarins clausenidin (1), nordentatin (2), clausarin (3), and xanthoxyletin (4) were isolated from the medicinal plant Clausena excavata. Recently, we found that 1 and 2 suppressed hepatitis B virus surface antigen in HepA2 cells, and in addition, 1-3 showed cytotoxic activity against four human cancer cell lines (A549, MCF7, KB, and KB-VIN). To explore the SAR of 1-4, 17 pyranocoumarin analogues (5-21) were designed and synthesized. Among these analogues, 5 and 10 were the most potent against hepatitis B virus with EC50 values of 1.14 and 1.34 mu M, respectively. The most interesting result in the cytotoxicity assay was the significant activity of 1, 5, and 6 against the multi-drug resistant cell line, KB-VIN, without activity against the KB cell line. These data suggest that these three compounds could be useful hits for developing MDR-inverse drugs. (C) 2009 Elsevier Ltd. All rights reserved.
• Claisen rearrangements-XIII
  作者：R.D.H. Murray、Z.D. Jorge

  DOI：10.1016/s0040-4020(01)82439-x

  日期：——